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Literature DB >> 20670018

Synthetic access to bent polycycles by cation-pi cyclization.

Abstract

The presence of an ether oxygen within a chain undergoing cation-polyene cyclization has a profound influence on the stereochemistry of this important construction, apparently due to nucleophilic participation of oxygen in the cyclization process and formation of an oxonium intermediate, leading to bent fused ring systems.

Entities: Chemical Disease Species

Mesh：

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Year: 2010 PMID： 20670018 PMCID： PMC2914341 DOI： 10.1021/ol101410g

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

6 in total

1. Enzyme Mechanisms for Polycyclic Triterpene Formation.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-08-18 Impact factor: 15.336

Review 2. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors: Ryan A Yoder; Jeffrey N Johnston
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

3. A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol.

Authors: Karavadhi Surendra; E J Corey
Journal: J Am Chem Soc Date: 2009-10-07 Impact factor: 15.419

4. A simple enantioselective synthesis of serratenediol.

Authors: J Zhang; E J Corey
Journal: Org Lett Date: 2001-10-04 Impact factor: 6.005

5. Total synthesis of (+)-alpha-onocerin in four steps via four-component coupling and tetracyclization steps.

Authors: Yuan Mi; Jürg V Schreiber; E J Corey
Journal: J Am Chem Soc Date: 2002-09-25 Impact factor: 15.419

6. Rapid and enantioselective synthetic approaches to germanicol and other pentacyclic triterpenes.

Authors: Karavadhi Surendra; E J Corey
Journal: J Am Chem Soc Date: 2008-07-09 Impact factor: 15.419

6 in total

9 in total

1. Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

Authors: Osvaldo Gutierrez; Jason G Harrison; Ryan J Felix; Fernando Cortés Guzman; Michel R Gagné; Dean J Tantillo
Journal: Chem Sci Date: 2013-10 Impact factor: 9.825

2. The Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol.

Authors: Michelle B Kim; Terrence E O'Brien; Jared T Moore; David E Anderson; Marie H Foss; Doug-Las B Weibel; James B Ames; Jared T Shaw
Journal: ACS Med Chem Lett Date: 2012-08-28 Impact factor: 4.345

3. Evidence that epoxide-opening cascades promoted by water are stepwise and become faster and more selective after the first cyclization.

Authors: Christopher J Morten; Jeffery A Byers; Timothy F Jamison
Journal: J Am Chem Soc Date: 2011-01-14 Impact factor: 15.419

4. Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Authors: Zachary Powers; Adam Scharf; Andrea Cheng; Feng Yang; Martin Himmelbauer; Takaaki Mitsuhashi; Lena Barra; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Ikuro Abe; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2019-09-25 Impact factor: 15.336

Synthetic access to bent polycycles by cation-pi cyclization.

1. Enzyme Mechanisms for Polycyclic Triterpene Formation.

Review 2. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

3. A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol.

4. A simple enantioselective synthesis of serratenediol.

5. Total synthesis of (+)-alpha-onocerin in four steps via four-component coupling and tetracyclization steps.

6. Rapid and enantioselective synthetic approaches to germanicol and other pentacyclic triterpenes.

1. Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

2. The Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol.

3. Evidence that epoxide-opening cascades promoted by water are stepwise and become faster and more selective after the first cyclization.

4. Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

5. Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

6. Synthesis of highly strained terpenes by non-stop tail-to-head polycyclization.

Review 7. Stereoselective Halogenation in Natural Product Synthesis.

8. A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework.

9. Bioinspired synthesis of pentacyclic onocerane triterpenoids.